Guo Tang

Name: 唐果; Guo Tang

Organization: Xiamen University

Department: Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering

Title: Associate Professor

TOPICS

Organic Chemistry

Azidation

Chemicals
References

Copper-Catalyzed Cascade Radical Addition–Cyclization Halogen Atom Transfer between Alkynes and Unsaturated α-Halogenocarbonyls

Co-reporter:Yuzhen Gao, Pengbo Zhang, Zhe Ji, Guo Tang, and Yufen Zhao

ACS Catalysis January 6, 2017 Volume 7(Issue 1) pp:186-186

Publication Date(Web):November 29, 2016

DOI:10.1021/acscatal.6b03033

A Cu-catalyzed cascade radical addition/cyclization/halogen atom transfer between alkynes and α-halogeno-γ, δ-unsaturated carbonyl compounds for the synthesis of various substituted cyclopentenes is described. Since up to four Csp3–Csp2 bonds, two Csp3–Br bonds, and two carbocycles can be established in a single reaction, this 100% atom-efficient reaction exhibits the advantages of wide substrate scope, high functional group tolerance, and step-economics, and it offers an entry of the atom transfer radical addition/cyclization (tandem ATRA-ATRC) process to the synthesis of substituted cyclopentenes.Keywords: carbon radical; copper-catalyzed; cyclic systems; cyclopentenes; tandem ATRA-ATRC reaction;

Phosphinodifluoroalkylation of alkynes using P(O)H compounds and ethyl difluoroiodoacetate

Co-reporter:Pengbo Zhang;Jianxi Ying;Yufen Zhao

Organic Chemistry Frontiers 2017 vol. 4(Issue 10) pp:2054-2057

Publication Date(Web):2017/09/26

DOI:10.1039/C7QO00466D

The first phosphinodifluoroalkylation of alkynes is achieved and the simultaneous addition of both difluoromethylene and phosphinoyl groups across the alkynes with high regio- and stereoselectivity is of great significance. By using palladium(II) chloride as a catalyst and Xantphos as a ligand, the reaction of P(O)H compounds, alkynes, and ethyl difluoroiodoacetate proceeds with moderate to high yields, and provides an attractive approach for the construction of (E)-γ,γ-difluoroalkenylphosphine oxides.

Direct synthesis of 2-sulfonated 9H-pyrrolo[1,2-a]indoles via NaI-catalyzed cascade radical addition/cyclization/isomerization

Co-reporter:Pengbo Zhang;Yuzhen Gao;Su Chen;Yufen Zhao

Organic Chemistry Frontiers 2017 vol. 4(Issue 7) pp:1350-1353

Publication Date(Web):2017/06/27

DOI:10.1039/C7QO00167C

Pyrrolo[1,2-a]indole and organosulfone are common structural motifs found in many pharmaceuticals. An efficient approach for the synthesis of 2-sulfonated 9H-pyrrolo[1,2-a]indoles via a NaI-catalyzed sulfonyl-radical-involved cascade cyclization–isomerization process is described. By using sodium iodide as a catalyst and tert-butyl hydroperoxide (TBHP) as an oxidant, various N-propargyl-substituted indoles and sulfonyl hydrazides are tolerated in this transformation, affording the corresponding products in moderate to good yields.

tert-Butyl Hydroperoxide Mediated Cascade Synthesis of 3-Arylsulfonylquinolines

Co-reporter:Liangliang Zhang, Su Chen, Yuzhen Gao, Pengbo Zhang, Yile Wu, Guo Tang, and Yufen Zhao

Organic Letters 2016 Volume 18(Issue 6) pp:1286-1289

Publication Date(Web):March 9, 2016

DOI:10.1021/acs.orglett.6b00198

3-Arylsulfonylquinoline derivatives play important roles as pharmaceutical drugs. A new method for the synthesis of 3-arylsulfonylquinoline derivatives has been achieved through tert-butyl hydroperoxide mediated cycloaddition between N-propargyl aromatic amine derivatives and arylsulfonylhydrazides without the addition of any metals. This transformation offers a straightforward route to the formation of a C–S bond and quinoline ring in one step via a sulfonylation–cyclization–aromatization process.

A Cascade Phosphinoylation/Cyclization/Desulfonylation Process for the Synthesis of 3-Phosphinoylindoles

Co-reporter:Yuzhen Gao, Guozhang Lu, Pengbo Zhang, Liangliang Zhang, Guo Tang, and Yufen Zhao

Organic Letters 2016 Volume 18(Issue 6) pp:1242-1245

Publication Date(Web):February 29, 2016

DOI:10.1021/acs.orglett.6b00056

3-Phosphinoylindole derivatives play important roles as pharmaceutical drugs and ligands. A new method for the synthesis of 3-phosphinoylindole derivatives has been achieved through silver-mediated cycloaddition between N-Ts-2-alkynylaniline derivatives and H-phosphine oxides. This transformation offers a straightforward route to the formation of the C–P bond, indole ring, and desulfonylation in one step.

Phosphorothiolation of Aryl Boronic Acids Using P(O)H Compounds and Elemental Sulfur

Co-reporter:Jian Xu, Liangliang Zhang, Xueqin Li, Yuzhen Gao, Guo Tang, and Yufen Zhao

Organic Letters 2016 Volume 18(Issue 6) pp:1266-1269

Publication Date(Web):March 2, 2016

DOI:10.1021/acs.orglett.6b00118

The first multicomponent reaction (MCR) involving aryl boronic acids, elemental sulfur, and P(O)H compounds is presented. It proceeds with excellent yields and provides an attractive approach for the construction of valuable S-aryl phosphorothioates and S-aryl phosphorodithioates using a one-step strategy. Moreover, this method can be easily adapted to large-scale preparation.

Cascade Phosphinoylation/Cyclization/Isomerization Process for the Synthesis of 2-Phosphinoyl-9H-pyrrolo[1,2-a]indoles

Co-reporter:Su Chen, Pengbo Zhang, Wanyun Shu, Yuzhen Gao, Guo Tang, and Yufen Zhao

Organic Letters 2016 Volume 18(Issue 21) pp:5712-5715

Publication Date(Web):October 25, 2016

DOI:10.1021/acs.orglett.6b02941

Pyrrolo[1,2-a]indole is a common structural motif found in many natural products and pharmaceuticals. A silver-mediated oxidative phosphinoylation of N-propargyl-substituted indoles was used to construct a variety of 2-phosphinoyl-9H-pyrrolo[1,2-a]indoles under mild conditions. This transformation offers a straightforward route to the formation of the C–P bond, cyclization, and isomerization in one step.

Copper-Catalyzed Cycloaddition between Secondary Phosphine Oxides and Alkynes: Synthesis of Benzophosphole Oxides

Co-reporter:Pengbo Zhang;Yuzhen Gao;Liangliang Zhang;Zhiqiang Li;Yan Liu;Yufen Zhao

Advanced Synthesis & Catalysis 2016 Volume 358( Issue 1) pp:138-142

Publication Date(Web):

DOI:10.1002/adsc.201500667

Copper-catalyzed cycloaddition between hydrogen phosphonates and activated alkenes: synthesis of phosphonoisoquinolinediones

Co-reporter:Ju Wu, Yuzhen Gao, Xin Zhao, Liangliang Zhang, Weizhu Chen, Guo Tang and Yufen Zhao

RSC Advances 2016 vol. 6(Issue 1) pp:303-306

Publication Date(Web):15 Dec 2015

DOI:10.1039/C5RA22570A

A new, general method for the synthesis of phosphonoisoquinolinediones has been achieved via copper-catalyzed phosphonation–cyclization of various methacryloylbenzamides with P(O)H compounds. This transformation allows the direct formation of a P–C bond and the construction of an isoquinolinedione ring in one reaction.

Synthesis of S-Aryl Phosphorothioates by Copper-Catalyzed Phosphorothiolation of Diaryliodonium and Arenediazonium Salts

Co-reporter:Liangliang Zhang, Pengbo Zhang, Xueqin Li, Jian Xu, Guo Tang, and Yufen Zhao

The Journal of Organic Chemistry 2016 Volume 81(Issue 13) pp:5588-5594

Publication Date(Web):May 31, 2016

DOI:10.1021/acs.joc.6b00925

Green methods for the synthesis of S-aryl phosphorothioates have been developed based on copper-catalyzed multicomponent reactions involving diaryliodonium/arenediazonium salts, elemental sulfur, and R2P(O)H compounds. Most target products are obtained with these two methods in good to high yields at room temperature. These transformations allow the direct formation P–S and C–S bonds in one reaction.

Mn(III)-mediated phosphonation–azidation of alkenes: a facile synthesis of β-azidophosphonates

Co-reporter:Jian Xu, Xueqin Li, Yuzhen Gao, Liangliang Zhang, Weizhu Chen, Hua Fang, Guo Tang and Yufen Zhao

Chemical Communications 2015 vol. 51(Issue 56) pp:11240-11243

Publication Date(Web):03 Jun 2015

DOI:10.1039/C5CC03995A

A new and general method for the synthesis of β-azidophosphonates has been achieved through Mn(OAc)3-mediated radical oxidative phosphonation–azidation of alkenes. The starting materials of P(O)–H compounds, alkenes, and azidotrimethylsilane are stable and cheap. This method can be easily adapted for large-scale preparation.

Mn(OAc)3-mediated phosphonation–lactonization of alkenoic acids: synthesis of phosphono-γ-butyrolactones

Co-reporter:Yuzhen Gao, Xueqin Li, Jian Xu, Yile Wu, Weizhu Chen, Guo Tang and Yufen Zhao

Chemical Communications 2015 vol. 51(Issue 9) pp:1605-1607

Publication Date(Web):08 Dec 2014

DOI:10.1039/C4CC07978G

A new, general method for the synthesis of phosphono-γ-butyrolactones has been achieved through Mn(OAc)3-mediated radical oxidative phosphonation and lactonization of alkenoic acids with H-phosphonates and H-phosphine oxide. Mn(OAc)3 can be readily prepared from Mn(OAc)2 in the laboratory. This transformation allows the direct formation of a P–C bond and the construction of a lactone ring in one reaction.

Copper-catalyzed tandem phosphination–decarboxylation–oxidation of alkynyl acids with H-phosphine oxides: a facile synthesis of β-ketophosphine oxides

Co-reporter:Pengbo Zhang, Liangliang Zhang, Yuzhen Gao, Jian Xu, Hua Fang, Guo Tang and Yufen Zhao

Chemical Communications 2015 vol. 51(Issue 37) pp:7839-7842

Publication Date(Web):31 Mar 2015

DOI:10.1039/C5CC01904D

The general method for the tandem phosphination–decarboxylation–oxidation of alkynyl acids under aerobic conditions has been developed. In the presence of CuSO4·5H2O and TBHP, the reactions provide a novel access to β-ketophosphine oxides in good to excellent yields. This transformation allows the direct formation of a P–C bond and the construction of a keto group in one reaction.

Mn(OAc)3-mediated arylation–lactonization of alkenoic acids: synthesis of γ,γ-disubstituted butyrolactones

Co-reporter:Yuzhen Gao, Jian Xu, Pengbo Zhang, Hua Fang, Guo Tang and Yufen Zhao

RSC Advances 2015 vol. 5(Issue 45) pp:36167-36170

Publication Date(Web):15 Apr 2015

DOI:10.1039/C5RA04429D

A general method for the oxidative cyclization of 4-alkenoic acids with arylboronic acids has been developed. The reactions described provide a novel access to γ,γ-disubstituted butyrolactones in moderate yields, and allow the direct formation of a C–C bond and the construction of a lactone ring in one reaction.

Cascade Arylalkylation of Activated Alkenes: Synthesis of Chloro- and Cyano-Containing Oxindoles

Co-reporter:Xueqin Li, Jian Xu, Yuzhen Gao, Hua Fang, Guo Tang, and Yufen Zhao

The Journal of Organic Chemistry 2015 Volume 80(Issue 5) pp:2621-2626

Publication Date(Web):February 6, 2015

DOI:10.1021/jo502777b

The general method for the oxidative cyclization of arylacrylamides with dichloromethane or acetonitrile has been developed. The reactions described provide novel access to chloro- and cyano-containing oxindoles in good to moderate yields that allow the direct formation of a C–C bond and the construction of an oxindole ring in one reaction. The use of a cheap and easily prepared Mn(OAc)3 represents an added advantage of this method.

Copper-Catalyzed Phosphonation–Annulation Approaches to the Synthesis of β-Phosphonotetrahydrofurans Involving C–P and C–O Bonds Formation

Co-reporter:Yuzhen Gao, Xueqin Li, Weizhu Chen, Guo Tang, and Yufen Zhao

The Journal of Organic Chemistry 2015 Volume 80(Issue 22) pp:11398-11406

Publication Date(Web):November 2, 2015

DOI:10.1021/acs.joc.5b02026

Substituted tetrahydrofuran derivatives play important roles as biological activities. A versatile method for the synthesis of β-phosphonotetrahydrofurans has been developed based on Cu-catalyzed difunctionalization of alkenes. This transformation would provide a new pathway for the formation of Csp3–P and Csp3–O bonds in one step. Furthermore, this copper catalyst system can be used in the synthesis of β-phosphonotetrahydropyrans and phosphono-γ-butyrolactones. These reactions were also performed well by using 3 equiv of Mn(OAc)3·2H2O as the oxidant without copper catalyst.

Tetrabutylammonium Iodide-Catalyzed Phosphorylation of Benzyl CH Bonds via a Cross-Dehydrogenative Coupling (CDC) Reaction

Co-reporter:Jian Xu;Pengbo Zhang;Xueqin Li;Yuzhen Gao;Ju Wu;Yufen Zhao

Advanced Synthesis & Catalysis 2014 Volume 356( Issue 16) pp:3331-3335

Publication Date(Web):

DOI:10.1002/adsc.201400436

Catalyst-free synthesis of cycloalkenyl phosphonates

Co-reporter:Xunfu Xu, Hu Chen, Yulei Wang, Yuxing Gao, Guo Tang and Yufen Zhao

RSC Advances 2014 vol. 4(Issue 28) pp:14740-14743

Publication Date(Web):12 Mar 2014

DOI:10.1039/C4RA00999A

The reactions described provide a facile and efficient access to cycloalkenyl phosphonates with good to excellent yields via Diels–Alder cycloadditions between alkynyl phosphonates and 1,3-dienes under catalyst-free conditions.

Experimental and theoretical studies on nickel–zinc-catalyzed cross-coupling of gem-dibromoalkenes with P(O)–H compounds

Co-reporter:Liu Liu, Ye Lv, Yile Wu, Xiang Gao, Zhiping Zeng, Yuxing Gao, Guo Tang and Yufen Zhao

RSC Advances 2014 vol. 4(Issue 5) pp:2322-2326

Publication Date(Web):21 Nov 2013

DOI:10.1039/C3RA45212C

A new stereoselective one-pot protocol for the preparation of E-alkenyl-phosphorus compounds under catalysis of an inexpensive nickel–zinc catalyst system has been developed, which provides a potential useful method for C–P bond formation. 31P NMR spectrum and density functional theory calculations were performed to study the reaction mechanism.

Synthesis of 6-Phenanthridinephosphonates via a Radical Phosphonation and Cyclization Process Mediated by Manganese(III) Acetate

Co-reporter:Yuzhen Gao;Ju Wu;Jian Xu;Xuerui Wang;Yufen Zhao

Asian Journal of Organic Chemistry 2014 Volume 3( Issue 6) pp:691-694

Publication Date(Web):

DOI:10.1002/ajoc.201402027

Abstract

6-Phenanthridinephosphonates have interesting biological activities and potential pharmaceutical applications. However, methods for preparing these compounds are very limited. In this report, dialkyl 6-phenanthridinephosphonates were synthesized through Mn(OAc)₃-mediated radical phosphonation of 2-isocyanobiaryls in good to excellent yields under relatively mild reaction conditions. As one of its notable features, the radical process allows the direct formation of a PC bond and the construction of a phenanthridine ring in one reaction.

Mn(OAc)3-mediated synthesis of β-hydroxyphosphonates from P(O)–H compounds and alkenes

Co-reporter:Yuzhen Gao, Ju Wu, Jian Xu, Pengbo Zhang, Guo Tang and Yufen Zhao

RSC Advances 2014 vol. 4(Issue 93) pp:51776-51779

Publication Date(Web):08 Oct 2014

DOI:10.1039/C4RA10593A

A new and general method for the synthesis of β-hydroxy phosphonates has been achieved through Mn(OAc)3-mediated radical oxidative phosphonation of alkenes with H-phosphonates and H-phosphine oxide. The starting materials of P(O)–H compounds and alkenes are stable and cheap. Mn(OAc)3 can be readily prepared from Mn(OAc)2 in the laboratory. This method can be easily adapted to large-scale preparations.

Direct Transformation of Amides into α-Amino Phosphonates via a Reductive Phosphination Process

Co-reporter:Yuzhen Gao, Zhongbin Huang, Rongqiang Zhuang, Jian Xu, Pengbo Zhang, Guo Tang, and Yufen Zhao

Organic Letters 2013 Volume 15(Issue 16) pp:4214-4217

Publication Date(Web):August 2, 2013

DOI:10.1021/ol4019419

The first general method for the reductive phosphination of amides in one pot has been developed. The reactions described provide a novel access to α-amino phosphonates in good to excellent yields, cover a broad scope of substrates such as secondary and tertiary amides, and do not require a low temperature.

Phosphorus oxychloride as an efficient coupling reagent for the synthesis of esters, amides and peptides under mild conditions

Co-reporter:Hu Chen, Xunfu Xu, Liu Liu, Guo Tang and Yufen Zhao

RSC Advances 2013 vol. 3(Issue 37) pp:16247-16250

Publication Date(Web):12 Jul 2013

DOI:10.1039/C3RA42887G

A mild method is described for the conversion of carboxylic acids into esters, amides, as well as peptides without racemization through carboxyl activation by the reagent combination of POCl3 and DMAP. Long chain alcohols could be converted to the corresponding ester in good yields. 31P NMR spectrum was used to detect phosphorus-containing intermediates in ongoing reactions directly, and a possible mechanism has been proposed based on these results.

Copper-Catalyzed Synthesis of -Hydroxy Phosphonates from H-Phosphonates and Alcohols or Ethers

Co-reporter:Zengxiang Zhao;Wanhua Xue;Yuxing Gao;Yufen Zhao

Chemistry – An Asian Journal 2013 Volume 8( Issue 4) pp:713-716

Publication Date(Web):

DOI:10.1002/asia.201201062

Copper-Catalyzed P-Arylation via Direct Coupling of Diaryliodonium Salts with Phosphorus Nucleophiles at Room Temperature

Co-reporter:Jian Xu, Pengbo Zhang, Yuzhen Gao, Yiyin Chen, Guo Tang, and Yufen Zhao

The Journal of Organic Chemistry 2013 Volume 78(Issue 16) pp:8176-8183

Publication Date(Web):July 18, 2013

DOI:10.1021/jo4012199

A new method for copper-catalyzed P–C bond formation through reaction of phosphorus nucleophiles with diaryliodonium salts at room temperature is described. Most target products are obtained with this method in high yields within a short reaction time of 10 min. It can be easily adapted to large-scale preparations. When unsymmetrical iodonium salts are employed, nucleophilic substitution occurs preferentially on the sterically hindered aromatic ring or the more electron-deficient ring.

KOH-mediated transition metal-free synthesis of imines from alcohols and amines

Co-reporter:Jian Xu, Rongqiang Zhuang, Lingling Bao, Guo Tang and Yufen Zhao

Green Chemistry 2012 vol. 14(Issue 9) pp:2384-2387

Publication Date(Web):20 Jun 2012

DOI:10.1039/C2GC35714C

The various imines were prepared from alcohols and amines in moderate to good yields under an air atmosphere promoted by KOH, eliminating the need for toxic transition metal catalysts. Due to its simplicity, this protocol will have wide application in synthesis.

Copper-Catalyzed Synthesis of Alkylphosphonates from H-Phosphonates and N-Tosylhydrazones

Co-reporter:Wenjun Miao;Yuzhen Gao;Xueqin Li;Yuxing Gao;Yufen Zhao

Advanced Synthesis & Catalysis 2012 Volume 354( Issue 14-15) pp:2659-2664

Publication Date(Web):

DOI:10.1002/adsc.201200295

Abstract

A new catalytic system for the alkylation of H-phosphonates and diphenylphosphine oxide with N-tosylhydrazones has been developed. In the presence of copper(I) iodide and base, H-phosphonates react with N-tosylhydrazones to afford the corresponding coupled alkylphosphonates in good to excellent yields without any ligands. Alkylphosphonates can also be prepared in a one-pot process directly from carbonyl compounds without the isolation of tosylhydrazone intermediates.

Ni(II)/Zn Catalyzed Reductive Coupling of Aryl Halides with Diphenylphosphine Oxide in Water

Co-reporter:Xinghua Zhang, Huizhi Liu, Xiaomei Hu, Guo Tang, Jun Zhu, and Yufen Zhao

Organic Letters 2011 Volume 13(Issue 13) pp:3478-3481

Publication Date(Web):May 27, 2011

DOI:10.1021/ol201141m

P-Arylation in water has been developed via cross-coupling of aryl halides with diphenylphosphine oxide (Ph2P(O)H) and (RP)-(−)-menthyl benzylphosphinate catalyzed by NiCl2·6H2O/Zn under relatively mild conditions.

-Aminophosphonates as novel organocatalysts for asymmetric Michael addition of carbonyl compounds to nitroolefins

Co-reporter:Qin Tao;Kan Lin ;Yu-Fen Zhao

Chirality 2008 Volume 20( Issue 7) pp:833-838

Publication Date(Web):

DOI:10.1002/chir.20552

Abstract

A cyclic α-aminophosphonate was found to be a novel organocatalyst for Michael type addition reactions of carbonyl compounds to nitroolefins to afford the corresponding adducts in high enantio- and diastereoselectivities. Chirality, 2008. © 2008 Wiley-Liss, Inc.

Copper-catalyzed tandem phosphination–decarboxylation–oxidation of alkynyl acids with H-phosphine oxides: a facile synthesis of β-ketophosphine oxides

Co-reporter:Pengbo Zhang, Liangliang Zhang, Yuzhen Gao, Jian Xu, Hua Fang, Guo Tang and Yufen Zhao

Chemical Communications 2015 - vol. 51(Issue 37) pp:NaN7842-7842

Publication Date(Web):2015/03/31

DOI:10.1039/C5CC01904D

Mn(III)-mediated phosphonation–azidation of alkenes: a facile synthesis of β-azidophosphonates

Co-reporter:Jian Xu, Xueqin Li, Yuzhen Gao, Liangliang Zhang, Weizhu Chen, Hua Fang, Guo Tang and Yufen Zhao

Chemical Communications 2015 - vol. 51(Issue 56) pp:NaN11243-11243

Publication Date(Web):2015/06/03

DOI:10.1039/C5CC03995A

Direct synthesis of 2-sulfonated 9H-pyrrolo[1,2-a]indoles via NaI-catalyzed cascade radical addition/cyclization/isomerization

Co-reporter:Pengbo Zhang, Yuzhen Gao, Su Chen, Guo Tang and Yufen Zhao